B is for Broken
by finstothefloor
Summary: When Blair's boyfriend admits his betrayal before her best friend has a chance to run from their mistake, the Queen B has some difficult decisions to make as her world begins to crumble and old habits return to threaten her sense of security and control. She always thought B was for Bold, but now it seems B is for Broken.
1. The Morning After

_**Chapter One: The Morning After**_

A loud, incessant ringing broke the still silence of the morning, crumbling the wild fantasies swimming through Chuck's mind. He had just been lounging at the Four Seasons with a drink in his hand and a particularly beautiful and poorly-clothed brunette rubbing lotion on her delicate skin for his amusement. With a particularly heavy sigh of regret, he broke through the last of his dreams, and his senses recognized the warm breath of another body next to his.

The events of the previous night replayed in his mind like an old picture film. He opened his eyes to find Serena Van der Woodsen curled up next to him, his red satin sheets covering her nearly-bare skin.

She had shed her glittery, gold excuse for a dress sometime between the elevator ride and his bedroom. The girl was efficient. As his eyes drifted over every visible inch of her curvy body, he understood what drew so many men into Serena's web. He would even admit she held a certain fascination to him. He always thought that, if the opportunity presented itself, he would not hesitate to explore the skillful wonders that made Serena's bedfellows so eager to return.

That had been before, he thought, amused by the twist of fate that landed an eager Serena in his bed at a time which he could not bring himself to take advantage. He had his reasons.

The ringing. Hadn't there been a ringing?

He glanced over at his nightstand to see his phone light up with a missed call. In fact, when he quietly reached over to grab his phone, he found he had missed several calls. Most of them were from Nathaniel, ranging from early evening to the call he had just missed. Those calls did not concern Chuck. Nate often plagued him with drunken phone calls – especially when he felt guilty.

But what had earned him a phone call from the Queen B herself?

Chuck felt a fluttering in his stomach as he saw her name. Damn that feeling. He decided to chalk it up to too much alcohol on an empty stomach. That was the only explanation.

If he applied logic to this mystery, Blair was more than likely calling to recruit him in her army for some new life-or-death scheme. Chuck found it incredulous at times that the most intelligent girl he knew could be oblivious to the goings-on in her personal life while meddling in the lives of everyone else. How could she not have seen Nathaniel's longing gaze wandering over her best friend? Chuck thought perhaps she did notice but disregarded the observations in favor of ignorance. The idea that perfect Nathaniel didn't love her and only her didn't quite fit into her little plan, did it?

Deciding to ignore his callers for now, Chuck continued to muse over the latest developments in the sordid lives of his fellow students until he saw Serena begin to stir, moaning as her senses came alive, likely torturing her with a pounding drum of a headache and a wild, churning ache in her stomach.

When she opened her cloudy blue eyes, she instantly met Chuck's amused gaze and froze. He watched, barely containing a wry grin, as she shot up and pulled a sheet to her skin, looking around the room as if she were searching for some kind of magical answer that could explain her current predicament.

"Wh- Chuck?" Her tone alone contained a burning question as to the night's events.

Chuck shifted to lay on his side, casually propping his head up with his hand, and allowing his wry grin to escape as he addressed her.

"Good morning, princess," he answered simply. He found great amusement in the emotions that ran across her face as she fought the heavy hang-over cloud withholding her memory.

"We. . .We didn't. . . Right?"

Desperation. Was he evil for loving this? Probably.

"If you're asking if we slept together, well. . . Then the answer would be yes," Chuck stated, allowing himself the small pleasure of seeing Serena's face crumble before he mercifully added, "But if you're asking if we had sex. . . Let's just say I demonstrated a heroic amount of restraint in turning you down."

He saw the relief pass through her as she sunk back down into the bed, pulling the sheets tighter around her. "If we didn't have sex, why am I half-naked in your bed?"

Chuck sat up too, crossing his bare legs casually. Serena pretended not to notice he wore only satin boxers and socks. "When I ran into you last night, I had three choices. I didn't think you'd like option one, which was dropping you off at Lily's, as charmingly drunk as you were. Was I wrong?"

Serena groaned. "No, definitely not," she relented. "Wait. . . What was the other option?"

"I could have left you with your dear friend Carter Baizen and allowed him to have his way with you," Chuck replied, stretching his limbs as he stood, pulling a robe from the floor tight around himself. Flinging Serena's dress at her from across the room, he added, "You're welcome."

Serena groaned again, sitting up and pulling the dress on over her head carelessly. "I was with Carter? God, how drunk was I? Okay, start at the beginning. I need to know everything."

"Well, Bart's gone on a business trip, so we have the luxury of privacy this morning." Chuck opened his bedroom door and gestured for Serena to follow as he headed toward the kitchen. "I'll make you the Chuck Bass signature solution to hang-overs while I tell you what I know."

Serena stole the sheet she had been wrapped up in and curled up on the couch as Chuck moved around the kitchen, placing a menagerie of ingredients on the counter. When he saw Serena's questioning gaze, he replied, "The recipe is top secret Bass property. Avert your eyes, and trust me."

Serena sighed heavily. "What is the world coming to? I'm trusting Chuck Bass after mysteriously waking up in his bed, half-naked."

"You're lucky my conscience kicked in," Chuck told her, winking at her seductively from the kitchen. "I was enjoying the company of some very lovely ladies when I noticed Baizen's hands drifting around your waist while you struggled to stand upright."

"So you came to my rescue like the gentleman you are?" Serena scoffed, then winced at the sound of her own voice.

"Your incredulity wounds me, S, really."

"It's not like we're the best of friends," Serena retorted easily.

"Maybe Baizen brings out the best in me," Chuck quipped, delighting in the strange sense of power he felt at being Serena's night in shining armor – more or less.

"Chuck. Be serious."

Bringing a glass of his mysterious concoction to the couch and sitting casually next to his half-naked sort-of friend, Chuck decided to tell her the truth of her situation last night. "Someone had to stop you from telling the entire club that you and Nate slept together."

Serena's hand had been in mid-air, reaching for the cup Chuck offered, when she froze. "What?" Her face paled, and she collapsed back against the couch, horrified. "Oh, God… Look, I was obviously really, _really_ drunk last night, so—"

"Save your pitiful attempt at lying for Blair, please," Chuck said, rolling his eyes and forcing the cup into her hand. "I saw you and Nate the night of the Shepard wedding."

Serena didn't respond, her eyes turning down to the floor, refusing to meet Chuck's gaze. She sipped from the cup, made a face, and took a quiet moment before responding. "Does Nate know that you know?"

"Ah, Nathaniel," Chuck sighed exasperatedly. "My poor, clueless best friend. No, he does not know that I know. Honestly, I expected him to break down and confess by now. He's not one for secrets. Not like us, huh, S?"

Serena's lip began to tremble, her eyes watering with tears. "He was going to tell her last night."

Very rarely was Chuck caught off guard by the actions of his best friend. Nathaniel was generally predictable. He had expected that his friend would pour his soul out to Chuck one night, seeking reassurance that keeping the secret was in Blair's best interest, which Chuck would probably have given – despite his mixed feelings on the subject. Then, Nathaniel would heed this advice and become a temporarily more attentive boyfriend to his naïve and unsuspecting girlfriend.

Yet… Nathaniel had jumped right into a confession to Blair.

 _Was that why she had called him?_

"I don't know if he did, for sure," Serena said, her voice turning hopeful. "I didn't exactly wait around to hear from him."

"I imagine that's why you dived headfirst into a bottle last night," Chuck said conversationally, the pieces clicking together in his head. Serena could be wild, for sure, but her most dangerous bouts of drinking often came after some sort of emotional impact. "Not that I blame you. If Nathaniel did in fact confess last night… Well, it's safe to say you've lost your position as the Queen's right hand."

Serena shot him a disgusted look. "You think _that's_ what I care about? My _rank_ at school?" she spat, though the malice didn't quite infect her tone the way Chuck was sure she'd intended. Her voice was too shaky, and the tears still swirling in her eyes were a dead giveaway. "I'm going to lose my _best friend_. This is going to destroy years of friendship. I don't think she'll ever forgive me."

Chuck hated the self-pity seeping into the girl's tone, pretending as if sleeping with Nathaniel hadn't been her choice. Poor Hurricane Serena – a swirling mess of accidents for which she couldn't possibly be held accountable.

"Tell me, S," Chuck began smoothly, containing the bitterness he didn't quite understand, threatening to color his words. "Was one night with good, faithful Nate worth it?"

Serena flushed. "I… I don't… No. Not if I lose Blair. And Nate."

She had hastily added the last part, but Chuck felt a strange significance in the addition.

"What did you expect to happen?" Chuck asked, incredulous. "Did you think Nathaniel would leave Blair for _you_?"

Serena's face was outraged – but Chuck caught the guilty gleam in her eyes before she hid it with anger. "I would never ask him to leave her! She's my best friend!" she defended.

"Yet you had sex with her boyfriend," he stated wryly, not following Serena's deluded train of logic. "Makes sense."

"It was a mistake, Chuck," Serena sighed dejectedly. "I don't know why I'm even talking to you about this. Like you have any right to lecture me about right and wrong. You're _Chuck Bass_."

"Touché," he allowed, smirking to himself. Arguably, he had done worse. Serena shifted on the couch, the sheet slipping as she did, allowing Chuck a peek at Serena's famously long legs – tanned and toned to perfection. Chuck did appreciate their beauty. He trailed a finger along the outside of her exposed thigh slowly. "Since I'm sure you're ever so _grateful_ to me for rescuing you…"

A perfectly manicured hand came down quickly to remove his. "Ugh, not _that_ grateful," Serena growled, standing abruptly, curling the sheet more tightly around herself as she hurried back to Chuck's room, presumably to find her handbag and shoes so she could storm out appropriately. Chuck smirked, picking her shoes up from where they had been thrown in a corner and heading to meet the blonde before she tore his bedroom apart searching for them.

"Well, you can't blame me for trying," he said calmly, holding up her shoes as he leaned in the doorway. "After all, I am _Chuck Bass_."

Serena rolled her eyes at him, snatching the shoes and storming past him back into the living room, where he watched her balance one leg at a time, pulling her heels on, while simultaneously searching for and successfully locating her handbag. Even hung-over and frustrated, the girl had a natural gift for multitasking with grace.

"I assume you can find the exit," Chuck called as he began to head back into his bedroom to resume the sweet dreams that had been taken from him so very early in the morning.

"Chuck…"

He turned and saw sincere gratitude on the face of the flustered damsel. She opened her mouth to awkwardly thank him, but the words froze in her throat as the elevator lit up, opened, and exposed the furious figure of the famously infamous Blair Waldorf.

Like a whirlwind, Blair stormed through the archway and greeted her stunned best friend with a slap across the cheek that forced Serena's head to the side and caused her to stumble.

A silence fell between the two girls. Blair's dark eyes glittered with betrayal. Serena clutched her cheek and stared apologetically.

Breaking the tense silence, Chuck poured himself a scotch. "Well, S, it's safe to assume he told her." 

_**\- Rise and shine, Upper East Siders. Queen B declares war early this morning with the slap heard 'round the world.**_

 _ **Look out, S. Queens aren't known to be forgiving. -**_

 _ **xoxo - Gossip Girl**_


	2. If Scotch Could Talk

_**Chapter Two: If Scotch Could Talk**_

" _I slept with Serena."_

She was dreaming. Definitely dreaming, Blair tried to convince herself. Any moment now, Audrey Hepburn would walk into her house and invite her to a glamorous party. Nathaniel would grin, declare his statement a decoy to distract her from the surprise, and whisk her into a ballroom-style extravaganza as the rippling edges of her dream slowly woke her. She would wake, and those words – those impossible, _painful_ words – would be just a fragment of a beautiful dream.

Blair clutched her fists, digging her manicured nails into her hand. If this were a dream, why could she not wake?

Nate's mouth was still moving, but the rest of his words fell into the air. That one sentence hung in the air like a heavy smoke, circling her, suffocating her.

" _I slept with Serena."_

"Stop talking," she demanded, and Nate was instantly quiet. Good, she thought. If he couldn't be loyal, he could at least be obedient.

This wasn't at all what she had been expecting when Nate called her and asked if he could come over tonight. She pulled her jacket close around her skin, adjusted her pencil skirt, no longer wanting Nate to see the expensive and carefully selected lingerie underneath that she had chosen when she thought…

Well, did it matter what she thought? She was a foolish girl, blind to the treachery that had been right beneath her nose. The strange expression she had noticed on Nate's face when Serena passed by them… The distance Serena had put between them recently… The constant displays surprising of affection from Nate…

He had been overcompensating.

This was real.

Like everything Blair ever wanted, Serena so easily swooped in and claimed it for herself. That she could find slightly – slightly – understandable. There had always been a competitive edge between she and her friend. Nate's betrayal, though, she could not fathom.

"Do you… love her?"

Nate hesitated, and Blair had to bite her lip to avoid reacting to the unintentional admission. "I… I don't know what I feel, Blair."

"Funny, because I'm not exactly sure what I feel either," Blair replied coldly, and her gaze turned him another three shades guiltier.

Even through the cold rage that seeped into her bones, she still ached to reach out and comfort the wreck of a boy in front of her. She could feel his sadness as deeply as her own, and somehow, that made this moment all the more unbearable. That she loved him enough to want to make _him_ feel better about his betrayal, while he obviously did not love her enough to avoid the betrayal in the first place.

She needed to distance herself from him now before she caved.

"Well, Nathaniel," she said, standing abruptly, blinking back the tears threatening her facade, collecting her bag and phone from the table. She would walk away from him with as much dignity as she could muster, regardless that she was leaving her home to run away from him. "Enjoy figuring that out _alone_."

"Blair—"

She felt his hand on her arm as she marched toward the elevator. Her entire body screamed at his touch, desperately wanting to turn and fall into his remorseful embrace, make him tell her again and again that he loved her and only her, make him say it was a mistake…

She jerked her arm away.

"You lost the right to touch me when you touched _her_."

In the elevator, Blair slid to the floor, unable to breathe. The tears she had been holding back were finally pouring over her eyelashes like a waterfall. She could taste the salt of her tears as she inhaled sharply. Nate, Serena… Everything was spinning. Everything was turning. She slammed the red button to stop the world from moving for just a second. She just needed a second.

"Miss Waldorf? Is everything alright?"

Reginald, one of the security officers. His voice rang through the quiet of the elevator like a gunshot. She was not alone. Someone had seen her.

"I'm… I'm fine," she called out, pulling herself up by the glossy, golden railings. She met her own eyes in the mirrored surface of the elevator doors and wanted to fall to the floor again. Her beautiful face was contorted in angst. Very unflattering, her mother would say. Her cheeks were streaked with grey tears as her mascara dripped. Was that acne forming on her chin? Her pencil skirt had ridden up and exposed the top of her thighs, and she noticed for the first time in months that she had gained at least ten pounds since her father had left. Her stomach felt bloated and full, churning with the array of emotions swirling in her gut. She was nauseous. She was disgusting. Simply, Blair Waldorf was a mess.

Why would Nate want her?

He wanted Serena… Beautiful, picturesque, playful, effortless Serena. She batted those perfect blue eyes, and the world was hers.

Blair's world was hers.

She had to take her world back, before she lost everything.

Slowly, Blair straightened her back, smoothed her skirt, and cleared her cheeks of tears. Blair Waldorf had too much to lose, and she needed a plan.

She needed Bass.

But, for the night, she needed a hotel room to fall apart in. The Palace would do.

~ . . . ~

When she rode the elevator up to the Bass penthouse the next morning, Blair expected to find a hungover Chuck Bass, cursing her for intruding on a morning tryst with his whore from the night before. Blair did not expect that that would be Serena.

All self-control flew out the window when the object of her anger was mere feet away. Blair didn't even have to think. For the first time in their entire friendship, Blair struck Serena… and effectively declared the end of said friendship.

"I knew you were a whore, S, but I didn't realize you were trying to set a world record," Blair spat, knocking Serena's shoes out of her hands pettily. "What would your new lover think about you shacking up with _his_ best friend? Or is that just the name of the game for you now?"

Her eyes darted to Chuck in the background. Stupid – yes, hungover – Chuck Bass. Why the hell did she have to be _here_? Why was she angry at Chuck too?

"You might want to get tested, Bass. Serena's making the rounds, apparently."

"Noted," Chuck winked, taking another swig of the golden liquid in his glass.

"We—we did not! Blair, I swear—" Serena seemed to be lost for words. Unfortunately, her body language spoke volumes more than her English.

"That you didn't sleep with my boyfriend?" Blair interrupted flatly. "Oh, please, Serena. We both know desperate lies don't go with that dress."

Chuck let out a low whistle.

"Shut it, Basshole."

"Blair, please," Serena pleaded, tears welling in her eyes. "We never meant for this to happen. Nate and I—"

"Stop talking," Blair hissed, advancing on Serena, forcing the taller girl to back into a wall. "You do not get to say his name. You do not get to talk to him. You no longer get to acknowledge his existence. We are not friends. You and Nate – not friends. I don't know why you have this desperate need to take things that don't belong to you, but let me remind you right now: Nate is _mine._ He is still mine, and I will burn your life to the ground for trying to take him from me. I know you like to break promises, but I promise I won't break mine."

The anger rolled off of Blair in waves of heat. She felt like she was seeing ripples in the air. She might pass out. Had she eaten today? She couldn't remember.

Serena cried pitifully in front of her.

"You're not leaving him."

Surprisingly, that came from Chuck. He set his scotch on the bar counter. His incredulous eyes met hers.

"Of course not," Blair declared, only deciding in that moment that she would not be giving Nathaniel Archibald up. She would not give Serena what she wanted. She would not let her world fall apart. If only the four of them knew, she could keep the pieces of her fracturing life together – even if the glue she used was threats, blackmail, and guilt. "Nate and I belong together. That hasn't changed just because slutty Serena offered him a moment of limited satisfaction. We are going to keep this secret. That means you, Bass," she said, glaring at him, crossing her arms over her chest. "I don't know how long you've been covering for Nate, but just keep pretending like you know nothing. That shouldn't be hard for someone with so few brain cells left."

"If you want to play games like a sad little doll, don't let me stop you," Chuck growled, reaching for the entire bottle of Scotch. "I'm Chuck Bass, and I have better things to do."

"Blair, we can't just pretend this didn't happen," Serena implored.

"Isn't that what you were going to do?" Blair retorted spitefully. Staring into the eyes of the girl she had grown up with, Blair felt a tug of weakness. She knew her friend was prone to impulsive mistakes. She defended Serena's mistakes, cleaned them up, and destroyed those who tried to hold them against her. For just a moment, Blair let the sadness of this betrayal seep into her next question. "Were you ever going to tell me?"

Serena looked down at the floor, and Blair knew her answer.

"I guess I know what our friendship really meant to you," Blair replied, holding her hands together to keep them from shaking. "Just as well. That will make it easier to dismantle this pathetic excuse for a life that you're living. I think I know just where to start."

Pulling herself back together, Blair waved ironically at Chuck. "Good day, Bass. It would have been fun to include you in the scheming, but clearly, you've hit your lowest low."

With a final glance at her ex-best friend, Blair Waldorf left the building.

~ . . . ~

"I didn't think I'd hear from you so soon," Nate said timidly, and Blair was pleased to see there was a glimmer of hope in his eyes. Hope for what, she wasn't exactly sure. That she didn't know made her nervous, stirring up the insecurities carefully concealed beneath her easily thousand-dollar make over.

She had texted him as she left the Bass penthouse last night, inviting him to brunch at Butter today. Well, 'invite' would be the wrong word, she supposed. She knew how to strongly imply that there would be consequences were he to stand her up. She needed to talk, and he needed to listen.

"Well, I know how much you love the food here, and it has been far too long since we've had a proper brunch date," Blair smiled cordially, taking a sip of her lemon and mint water to wash down the things she wanted to say.

"Are you… okay?" Nate asked cautiously. "You do… remember the conversation we had?"

"Of course, my love," Blair said sweetly. "One can hardly forget the sharp stab of a knife to the back. However, I have decided to forgive you. Conditionally, of course."

Nate's eyes were wide. "Just like that, you've forgiven me?"

"Ah, ah, ah," Blair corrected lightly. "As I said, I have conditions."

"Conditions," Nate said slowly, turning the word over in his mind. He had dated Blair long enough to know that was a dangerous word. "Blair, I'm not going to help you hurt her."

He would instantly jump to her defense. After all of the pain that she had caused them, he would still jump to save Serena from Big Bad Blair. Blair clenched her teeth to keep herself composed.

"We are not going to discuss her," she said, through gritted teeth. "That's one of my conditions. Naturally, any mention of her will be distressing to your loving girlfriend, who is struggling to forgive you and allow her love for you to overcome her distaste for your discretion. So, the first condition: Serena is dead to you."

Nate looked torn. "Wait, you still want to be together? After what I did? I don't understand," he said, ruffling his perfect hair in exasperation. "Why do you want to forgive me?"

Blair took his hand, gently, and stared him down. "Nate, I love you. More importantly, we are meant to be together. What we have has been built over a decade of childhood kisses and silly games. But this is no longer a game. I hate what you've done, but I can forgive you. If you promise to honor my conditions, I will force myself to forgive you, and we can go back to being the King and Queen of the Upper East Side."

"And your first condition is that I never talk to Serena again," Nate said, pulling away from her and staring at the street outside. "Blair, I don't know if I can do that."

"Well, then," Blair said, softly, handing him a menu. "Let's enjoy what might be our last brunch together."

With a strange glimmer in those hopeless eyes of his, Nate sighed. They both mulled over their menus. Their waiter came to refill their glasses – Blair had completely emptied hers already – and they ordered their food. Nate was surprised Blair ordered only their seasonal fruit, but she told him she had lost her appetite. He eyed her with concern.

"Don't worry about me," Blair said sadly. "Soon, I won't be your problem anymore."

She looked down at the table and was surprised to feel Nate grab her hand.

"What are the other conditions?" he asked.

Blair smiled.


	3. Secrets Don't Make Friends

_Greetings, Gossip Girl friends. I just want to thank you all for supporting this story thus far! I've had many people express their interest in Chuck's perspective, and I'm happy to say you'll get plenty of that. Hang in there, guys. Things haven't even begun to ramp up yet. xoxo_

* * *

 _ **Chapter Three: Secrets Don't Make Friends**_

Chuck Bass took immense pride in always being one step ahead of his adolescent friends. Generally, their secrets weren't all that complicated. High school secrets, even among the Manhattan elite, revolved around juvenile heartbreak, meaningless competitions, and petty gossip. The toxicity of the school environment was fueled by gossip, and the arrival of the unknown and omniscient Gossip Girl set the thirst for dirt ablaze amongst his fellow students.

Chuck loved Gossip Girl for this reason. She made it that much easier for scandalous information to surface. He continued to stay one step ahead of his classmates, while exploiting this new resource and kindred spirit to stumble upon other secrets. He excelled in the pursuit of secrets – just as he did in the pursuit of women. He believed his cavalier approach helped him with both.

Skulking in the background at school, infamously playing as his role, Chuck saw what others could not.

He saw Blair's minion, Penelope, swipe an expensive lip gloss from Stacy Bradshaw's purse during the Memorial Day picnic, then proceed to tell all her preppy friends that it was the newest shade straight from Milan.

He saw athletic star Kyle Minnick sneak behind the bookshelves in the library during finals to down a handful of pills while no one was looking, then focus with a drug-induced intensity while Dustin Whitaker struggled to teach him basic trigonometry for the fourth time this week – probably in exchange for some of those pills, if Chuck believed the stoners he smoked with behind the school courtyard.

Chuck saw the first time that Serena van der Woodsen averted her eyes to conceal her jealousy as Blair planted a chaste kiss on her boyfriend's lips. He watched Nathaniel longingly stare after the blonde as she walked away, leaning slightly out of his girlfriend's embrace as he did so.

He saw Blair see this too. Yet the astute girl dismissed the reality before her eyes. Obviously, these details did not fit into her neat little world. Chuck wasn't sure if he envied Blair for her blissful ignorance, or if he pitied her for resorting to it. Then again, he wasn't one to waste energy on emotions like pity.

Regardless, Chuck knew that this tentative balance between his friends would not last. The night of the Shepard wedding, his instincts were proven right. He supposed he should start putting money down on these things. He would be a fucking billionaire by now – by his own right, not his father's.

This morning, Chuck leaned against the brick wall facing the courtyard, accompanied by two of the school's resident stoners. He was relaxing into a nice morning high and took another puff, blowing smoke into the air and smirking at the disgust on the faces of some of the Constance girls passing by. He knew at least two of them personally – very personally – and knew exactly how he could replace the disgust on those painted faces.

Chuck embraced the high, letting it distract him from the hangover, and surveyed the courtyard, his dark eyes searching for drama. He glanced toward the steps where Blair's minions sat, whispering conspiratorially to themselves. Surely something of interest there.

That's when Chuck realized what he had not seen this morning – or rather, who.

The Queen B and her remorseful boyfriend.

Just as his curiosity peaked, his phone buzzed; his kindred spirit answered his question.

 _ **I hear a little Butter goes well with truancy. Looks like Constance's 'It Couple' is enjoying a little rebellious behavior. So why does B look so sad? Trouble in paradise?**_

Accompanying the blast was a photo of Blair and Nate in a private booth at Butter. Gossip Girl was right; Blair looked devastated as she stared down at her menu. She wore a yellow floral shift dress that Chuck recognized as an Eleanor Waldorf original and a shiny pearl hairband, pushing her dark curls away from her face. He noticed the way her right hand tightly clutched her glass, as if it held her world together.

Nate was looking at her with an expression could only describe as conflicted.

Neither were wearing their school uniforms, so Chuck wondered if they planned to show up to class at all today. Skipping school was highly unusual for the pair and would not go unnoticed. More importantly, was this an end-all brunch – or a reconciliation?

"Serena! Serena!"

Penelope, Kati, and Hazel jumped off the steps as soon as they spotted the van der Woodsen driver drop Serena and Eric off at the school entrance. Eric instantly darted away from his sister, who tried to duck her head and avoid the gaggle of gossip-ready girls.

"Serena, wait!"

"I bet you know why Blair's not here," Penelope said in a sing-song voice. "Come on, S. Spill. Is she pregnant? Oh my God, I bet she told him she's pregnant."

"I didn't even know she and Nate had sex!" Hazel exclaimed, looking hurt.

The girls had been trotting alongside the thoroughly-frustrated Serena, who finally spun around. Effortlessly, she smiled and shared a knowing look. "Ladies, ladies. B is so not pregnant. You know she's more conscientious than that," she said, winking, but not denying the idea that Blair and Nate had slept together.

The exact sort of subtle confirmation that the girls needed to latch onto a different topic – the secret of when exactly Blair had lost her virginity to the charming Archibald boy.

"Oh my God, she lost her V-card and didn't tell us?" Hazel exclaimed.

"Then why does she look sad in that picture?" Kati asked.

"I would be sad too if I had to leave that body for even a minute," Penelope sighed. "Blair is so lucky. We are so getting the deets when she's back."

"What if they did it last night? And then he takes her to brunch? God, Nate's so classy!" Kati gave a dreamy sigh too.

The girls kept chattering, completely missing the pain in Serena's expression as she listened to them talk about Blair and Nate's epic romance. Serena met Chuck's eyes for a moment, a knowing look passing between them. Chuck blew smoke in her direction and nodded for her to join him by the wall. She rolled her eyes and started to walk away.

Chuck handed his joint to one of the boys by the wall. "Get rid of this," he ordered casually.

He followed Serena. "So," he whispered in her ear once he was close enough. They were walking down the hallway towards the girl's lockers. "Were you conscientious too?"

The fury on Serena's face was terribly attractive. "Why don't you tell me, Chuck? Since you were watching us like a creep."

"Creep is such a strong word," Chuck replied, grinning. "I was just watching out for a dear friend."

Serena opened her locker with a little too much force. "If you're such a good friend, why didn't you tell Nate you knew? Why did you let him suffer with this secret alone? This has been tearing him apart." Serena grabbed a binder from the locker and slammed it closed. "Seems like Chuck Bass is only ever watching out for Chuck Bass."

This gave Chuck pause. He truly believed Nathaniel would drunkenly confess his affair with Serena to him before ever considering telling Blair. He had observed his friend's guilt manifest itself in jewelry, flowers, and public displays of affection. He saw Nate throw himself into sports and aggressively run around the track until he looked ready to pass out from exhaustion. Usually, the party phase followed – which was when Chuck learned what secret Nate was so actively trying to outrun.

Had he been wrong to let Nate handle this alone? Was that being a bad friend?

Damn Serena for making him think so hard.

"If all you're going to do is torture me, then go away, Chuck," Serena said, pushing past him.

Chuck grabbed her arm, causing her to spin around defensively. "If you want me to do more, all you have to do is ask," he purred, just wanting to ruffle her pretty feathers for questioning his friendship with Nate. "It's not like Nate won't already think you've had a taste of Bass after Blair gets through with him."

Serena's face paled; that Nate might think she had slept with Chuck had obviously not crossed her mind.

"Excuse me," a tan, dark-eyed boy with a bush of curly hair interrupted, placing a hand on Chuck's arm. "But I think you need to leave her alone. Now."

Chuck thought his name was Humpty or Hurley or something equally common. The boy was there on scholarship – meaning he was beneath the station of someone like Chuck Bass.

Yet, here he was with his hand on Chuck's arm.

"I think you need to remove your hand before I'm forced to learn your name," Chuck warned. "That will be unpleasant for us both."

"Dan, it's okay," Serena said, meeting the boy's concern with a gentle smile.

"Does your sense of entitlement come with bad hearing? Let go of her," Dan demanded, ignoring Serena's placation.

"I'm told those of us who are entitled should be charitable to those less… fortunate," Chuck replied, glancing pointedly at Dan's rugged messenger bag and clearly discount shoes. "I'll see you around, S. I hope you dump the trash on your way to class."

Chuck almost pitied the poor sap who was falling into the ever-growing line for Serena's affections. Almost. The boy was bolder than he had any right to be, and that grated on Chuck's nerves like nails on a chalkboard. Dig up dirt on Dan, Chuck noted to himself. He needed to learn his place in New York society. Chuck happened to be an excellent educator.

The school bell rang, and students scattered quickly. Everyone but Chuck. He would make his way to Literature in his own time. There was no rush.

After all, he was banging the teacher.

~ . . . ~

Try as he might to ignore it, Serena's accusation had hit a nerve with Chuck. He wasn't sure what state Nate would be in after his brunch with Blair, but he was sure his friend could use an ear and a drink. Hopefully Chuck could talk to him about Serena spending the night at his place before Nate got the wrong idea. If Nate truly had feelings for Serena, then Chuck supposed having sex with the girl was breaking some sort of guy code – even if Nate had a girlfriend who wasn't said blonde bombshell.

Then again, that code had always been a little fuzzy.

It had taken over an hour for Nate to text back, but he agreed to meet Chuck later that night at the Keybar in East Village. Chuck planned for them to hit a few different bars and clubs, but as always, it would depend on exactly how drunk Nate was willing to get.

"Father, you're home," Chuck said in surprise as he stepped off the Palace penthouse elevator. Bart Bass sat in the foyer, grey power suit and all, thumbing through some papers. His cell phone sat on his knee, which was bouncing impatiently. Chuck knew that his father was still in work mode, meaning his presence would not be welcome.

That wasn't unusual.

There were other people in the penthouse. Chuck noted two men and three women in the kitchen, scurrying around.

"Yes, hello," Bart said dismissively. "I have business associates coming here for dinner in two hours. Please make yourself scarce by then."

"Of course," Chuck replied, squashing the disappointment in his stomach. Why had he expected any different from his distant father? "I'll make sure to take my whoring far from your distinguished guests."

"I'd rather not embarrass the Waldorfs and van der Woodsens when you stumble upstairs drunk with their daughters," Bart said quietly, not even looking up from his papers. One of the caterers in the kitchen paused, trying to listen. Chuck glared at her, and she suddenly became very interested in the tile pattern on the kitchen floor.

"Unfortunately, I am not sleeping with Blair or Serena. Not for lack of trying."

"Lucky girls."

Chuck went to his room to change out of his school clothes. He had hours to kill before Nate could meet him, but he certainly would not spend another moment of that time in a home where he wasn't wanted. Someday, Chuck expected his skin to thicken, and his heart would stop aching every time Bart Bass dismissed him.

Someday.

"This is me, making myself scarce," Chuck said, waving a hand as he walked past his father, trying not to meet his father's eyes. "Goodnight, Father."

Bart Bass did not respond.

~ . . . ~

"Well, well, well, looks like my influence has finally rubbed off on you," Chuck greeted Nate when he finally arrived. The music at the Underground was loud, and Chuck had to raise his voice. "Skipping class is such a Bass move."

Even in the dim, blue lighting of the club, Chuck could easily see the stress on Nate's face. A thinly-clad, bustily-gifted brunette appeared to bring Chuck the scotch he had ordered, and Nate requested their strongest drink. Chuck thought that was a bad sign.

"Blair said you know," Nate said as the girl walked away.

Guilt churned in Chuck's stomach in an unfamiliar way. "I figured you would tell me when you wanted to talk. That's how this works, right?"

Maybe Nate sensed the apology and uncertainty in his tone, because he gave a weak grin. "Yeah, that's how this works. I can't believe the mess I've made."

"I can. You've had your eyes on S since we were kids. Your parents pushed you towards Blair."

Nate's drink arrived, and he downed it as quickly as it came. "You know, Blair wants to forgive me. I cheat on her with her best friend, and she wants to forgive me. She has conditions – because she's Blair – but she wants to forgive me. Is she crazy?"

"Certifiable," Chuck replied easily. "The biggest question is: do you want to be forgiven?"

"I don't know, man. Can we just drink?" Nate asked, obviously overwhelmed.

Knowing Nate was easily overwhelmed, Chuck got them another round. Then, he got them two or three more. Chuck just wanted to distract his friend from his troubles, and it seemed the distraction was working. Nate kept stumbling to the dance floor, trying to hit on a sexy blonde in a thin silver romper, dancing around her like a fool. Chuck enjoyed seeing his friend unwind. Unfortunately, when that blonde's boyfriend arrived and got in Nate's face, Chuck decided it was time to call his driver.

"You can't take me home," Nate slurred. "My mom'll be sooooo mad."

"Just get in the limo," Chuck said, pushing Nate into the backseat. "There are plenty of rooms at the Palace."

"I have to choose Blair," Nate said suddenly, probably louder than he intended. "I want Serena, but I've gotta choose Blair."

"You're rich, Archibald," Chuck remarked, sipping from a crystal glass in the back of the limo, almost accentuating his point. "You don't have to do anything."

"But I'm not," Nate confessed. "My parents… They need Waldorf money. You don't understand. I have to make things work with Blair. It's always been the plan."

"Times have changed, Nate. Women don't come with a dowry anymore," Chuck said. "I think you need more to drink."

Nate sighed and accepted a glass from Chuck. "Blair is too good for me. She deserves better."

"Maybe. You deserve to get what you want."

"Maybe," Nate sighed, leaning back into the seat to finish the glass. "Maybe."

Chuck watched his friend fall asleep in the back of the limo, and he could not tell if Nate was more or less stressed than when the night began. If there were truth to Nate's claim, that his parents depended on Waldorf money for some reason, then he knew Nate was bound to Blair indefinitely.

Nate Archibald was a dutiful son to the Captain, following every plan laid before him without question. He was the kind of son he knew Bart wished he had. Chuck was certain that Nate would chop his own arm off and gift-wrap it if he was asked. Loyalty was wonderful and all, but shouldn't one's own happiness take priority?

And if Chuck was a good friend, shouldn't he fight for Nate's happiness?

Well, Blair Waldorf wasn't the only one who could scheme.


End file.
